Boo Club Memories

(Usual Disclaimer Time: All the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun.)

(Author's Note: This story requires a little explanation before we get too deep into it. Book Club Memories is a much-requested spin-off tale from my vaguely epic story Senior Year Memories, taking place between chapters 40 and 41 of that tale. All of you who have read that far in the story will hopefully enjoy the continuation of various storylines, but as for the rest of you, I want to let you know now that it is NOT necessary to be a Senior Year Memories expert to enjoy this story. I'm doing my best to write it as both a continuation, and a story that will stand on its own for your reading pleasure. I hope you all enjoy!

Further, I would like to thank the readers whose votes helped determine some of the action of this story, as well as helping create the character of Mrs. Cassandra Pruitt. As always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories.)

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FRIDAY

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We'd been on the road for about an hour and a half, and by the reckoning of Lauren's GPS, we'd nearly reached our destination. The suburban landscape of Regan Hills, California had given way a while back to that empty sort of infill you get once you get out of the bigger cities in SoCal, with outlet malls, big box stores and highways as far as the eye could see. A while past that came some semblance of rolling hills and a forest's edge, with small towns and family farms our new landscape.

Where we were now, though, was just forest, plain and simple.

"Looks like the kind of place you'd film a horror movie," I mused, looking out the window to see the late afternoon light still somewhat filtering through the evergreen trees. "You know, the kind where a bunch of nubile camp counselors looking to get laid are stalked by a masked psycho from behind the trees with something sharp in one hand and a whole lot of Freudian excuses in the other? I'm not saying that's definitely going to happen or anything, I'm just noting that... well, that it looks like it *could*."

"You've got one hell of an imagination," Lauren said.

"I've had this accusation thrown at me before," I admitted.

"And more than that... you need to get out more, Ryan," she continued, flashing her brilliant, toothy smile. "The world's not out to get you, and there's more out there than just city, you know."

I grinned. "I'd have to convince my dad to buy me a car first."

My dad had nothing against me driving, and I did already have my license, but he said he wanted to wait for the right moment before getting me a car. I didn't know what that right moment might be, but, it felt like it was still a ways off.

"Have you thought about getting an afterschool job? Getting a car on your own?" Lauren suggested.

"I have, but with schoolwork and finals up ahead and the school newspaper... I don't know where I'd find the time these days," I admitted.

Lauren smirked. "And those are the *only* reasons you don't have time?"

I laughed. "I mean, my social calendar was a lot fuller this year than I had expected."

"I'd bet. Mine has also been unexpectedly busy... and I think I have you to blame for some of that," she said.

"I haven't heard you complain," I said, looking at her.

Lauren kept her eyes on the road, but her smile broadened ever so slightly more. "Oh... I would never complain about your attention, Ryan... but let me know if you want help convincing your dad on the car situation. I could always bust some heads, put the screws to him for you."

"I'm sure you would... but I'll be fine. I'll get my car when I get my car," I said.

"Alright," she shrugged, "But if you change your mind, again, head busting, I can do it; I'm stronger than I look!"

I smiled, knowing well that she could. Mrs. Lauren McNeil was an old family friend, as she was my best friend, Tori's, mother, and since Tori and I were pretty well attached at the hip as kids, she was pretty well almost always there for the ride. I'd looked up to her as a surrogate mother figure of sorts at first, in those years after my own mom died, and later she might well have been one of my first crushes. I always knew her as a strong woman, capable of doing anything she wanted to no matter the opposition, and I didn't doubt she could "bust some heads" if she really wanted to.

At 5'11" (taller when she wore her heels, as she usually did), and very fit for a woman in her early 40s, Lauren was a fairly imposing woman on physicality alone, but when you looked at her and took in her beauty... she could be downright intimidating. Her youthful, gorgeous face with its high cheekbones and porcelain skin could easily light up with her bright smile, or easily break you with one harsh look from her cool, blue-green eyes. Her hair, long, straight and shimmering red, so soft you wanted to run your fingers through it, fell to her mid-back, and was currently tied back with a simple hair tie. As a woman who generally favored casual clothing, or corporate chic, it was interesting to see her wearing something in between these two styles today, with a light blue, knee-length skirt, and a pale yellow, short-sleeved button-up blouse that positively strained over her ample chest.

Yeah, it was hard not looking at her throughout the ride, but given the smiles she shot my way periodically, I knew she liked these glances.

We'd made it for most of the ride like this with small talk and listening to the radio, but now that we were getting closer, it felt like it might be time for some more pointed discussion.

"So... do you guys do this often?" I asked.

"Retreats? Not... not very often," Lauren explained. "We try to get book club meetings going once a week or so, but long weekend retreats like this we can only usually manage once a year or so. It's hard getting everyone's schedules together, and finding a good rental house like this at a decent price..."

Her voice held some nostalgia, and more than a little of something pleasantly darker. Lauren shivered in her seat slightly, her cheeks blushing as her eyes sparkled with a certain naughtiness.

Knowing what I knew about this "Book Club", that wasn't all that surprising. I'd come to know a handful of this club's members over the course of senior year, and had gleaned enough details to know that there was more to this book club than reading a recent bestseller and bitching about their husbands over glasses of rosé.

No, the leader of this club, Viola Kent (mother of another of my good friends, Sarah), had done well over time to evolve the club into something considerably more... unique, I guess you'd say.

Officially, Viola would have called herself a self-employed dance instructor and entrepreneur, running a number of lucrative side hustles out of her home. Unofficially, she was a retired stripper who these days made some serious cash teaching pole-dancing classes and selling sex toys, a side business that had seeped its way into the book club she ran.

What started out as just a new venue to make money had become, in time, a way for a number of the wives and mothers of Regan Hills to get together and fool around with each other, relieving stress and getting laid when those opportunities had proven few and far between.

By what I had been told, I was likely the first man to have ever been invited to one of their meetings, let alone their long weekend getaway. Knowing as many of the ladies who'd be attending as I did, I wasn't that nervous, but I'd be lying if I said there weren't some butterflies in my stomach.

"I know I've probably asked this a million times already, so if I'm being annoying, I'm sorry, but you're all certain it's cool for me to be here, right? I mean, Viola invited me, but I don't want to be intruding, you know?" I asked.

Lauren laughed, softly. "Relax, Ryan. The other ladies are dying to see you... I think you're going to be the belle of the ball, honestly. Or would it be beau of the ball? I'm not even sure that's a thing, but it might be somewhere. Who cares, really... you're going to be popular. You better be ready, though, you know these are going to be a hard four days, right?"

Now it was my turn to laugh. "I can handle it."

"You say that now, but you don't know what these ladies are like unleashed. You've only seen some of them before, and one on one at that... get us together, and things can get a little crazy," Lauren explained, smiling at me with a hint of mischief.

I wasn't sure if I was meant to be frightened or intrigued by this description, so I asked, "Only a little crazy?"

She rolled her eyes. "Okay, very, very crazy... hot and wet and sweaty and... look, I could try to describe it, or you could see it for yourself. It won't be that much longer."

"I guess not," I said, eying the GPS. The road around us had become a well-maintained dirt path some time ago, and things were beginning to feel quite isolated, but it said we were close to our destination.

"In fact..." Lauren replied, looking behind her briefly before pulling her car over to the narrow shoulder to our right. She turned off the engine, then looked at me. Her breath was increasing ever so slightly, the flush that had started in her cheeks spread as she bit her lip.

"Yeah?" I asked, grinning with anticipation.

"I don't know how much time I'll be able to have you to myself this weekend... there are a lot of ladies, after all, who want to vie for your time... what would you say if I suggested we spend a little time in the backseat before we made it to the cabin?" she asked, fluttering her eyelashes at me and smiling a hopeful, vaguely silly smile.

I didn't say anything, because I didn't have to say anything.

I stepped out of the car briefly, before reentering through the passenger side rear door. Lauren soon followed, sliding in and sitting next to me. Without a center console between us like in the front seat, there was nothing stopping us from sliding up next to each other. Nothing stopping us from getting a *lot* closer, honestly.

Lauren looked at me, hopeful.

I leaned in and kissed her. Her full lips melded against mine in a familiar fashion, her mouth soft and eager as she moaned against my lips. Her hands, quick and strong, fumbled for my belt and began to undo my pants, while mine soon found their way onto her blouse. When someone like Lauren McNeil wants you to grope her chest, some of the softest, roundest DDDs in the world, you take that opportunity.

So, yeah, I squeezed her tits while we made out, feeling her firm nipples poking through her top as she continued moaning and writhing against me. Finally, I did find those buttons, opening up her top and pulling out her bra-clad tits. The need to see her breasts brought a primal side to me, one that couldn't be fought easily, and was enough to make me break the kiss.

"Mmm, it's been too long since you've seen these, hasn't it?" Lauren purred, toying with the heavy-duty clasp at the front of her bra.

Silently, I nodded. She grinned, undoing the clasp and freeing her massive, perfect tits for me. Her nipples stood out rock-hard and begging to be sucked on, and... well, I wasn't one to pass up opportunities like that, not anymore.

And so I ducked down, kissing and licking and suckling at Lauren's tits, making her moans take on a higher, more desperate tone as we furiously grabbed at each other. She'd finally gotten my belt undone, then unbuttoning and unzipping the front of my jeans. I could feel one of those swift, strong hands of hers rubbing my large erection through my underwear, her moans now taking on a lower sound of appreciation and anticipation.

"So big... oh, I've needed this again... I've needed this for so long..." Lauren moaned, finally pulling enough of my underwear down to fish out my very hard, very large cock.

Admittedly, it's not to everyone's taste, but having a thick, ten-inch-long cock had made my senior year a lot more memorable than it might have otherwise started out as. I'd been blessed to have found myself with a number of women who were more than happy to play with such a monster appendage, and lucky for me, Lauren was particularly talented when it came to handling such big cocks.

Her hand slowly trailed up and down my shaft, cupping the thick head and running her thumb over it until she could coax out a bead of precum. My lips still wrapped around one of her nipples, I hissed as she began to spread that precum around, that bead soon becoming a steady flow at her instruction as she began to expertly jack my cock. She was good at this... *real* good at this, so good it was taking a lot of restraint to not just let loose here and now. Lauren really knew how to work a cock, and if I did nothing but sit right here, sucking on her tit and letting her jack me off, it would only be a matter of minutes before she had me cumming.

Well, two could play that game.

With a free hand, I reached beneath her skirt, feeling a pair of lacy panties that barely covered her pussy. There was a distinct, moist heat coming from behind them, and Lauren moaned quite lustily at the slightest contact that I made.

I let her nipple pop from my mouth and grinned up at her as I pushed her panties to the side and began to finger her hot, needy pussy. Lauren's mouth dropped open as she leaned her head back against the seat, moaning and writhing as she rocked her hips against my fingers. I may not have had the decades of experience with sex that she had, but I'd had one hell of a year, and had become quite familiar with how to make a pussy feel good. I explored her outer folds, running light yet firm circles over her clit for a while, before delving deeper and fucking two fingers in and out of her impressively tight cunt, before pulling out and repeating the process again.

I teased her every bit as much as she teased me, toying with her, getting her close to the edge and not letting her cross it. We sat side by side like this for some time, pleasuring each other with our hands while occasionally exchanging deep, lusty kisses as we tried to see who broke first.

This would prove an interesting contest, particularly because this wasn't the first time Lauren and I had been in more or less this exact position. We knew each other's bodies well and how to make each other feel deliciously good, but we also knew how to play the long game. I knew she wanted some time where she could keep me to herself before we arrived at the getaway, and I was more than happy to indulge her.

I mean, how could I not?

But even in as ecstasy-inducing a battle of wills as this, someone was bound to break eventually.

"Oh god..." Lauren mewled, whining and looking at me with such beautifully needy eyes. "...if you keep doing that, I'm going to cum..."

"You want that?" I asked, grunting as I did absolutely everything I could to put off my own orgasm.

She bit her lip in consideration, then shook her head. "I need you inside of me when I cum. Please, Ryan?"

She didn't have to flutter her eyelashes with such a sweet desire to fuck the life out of me to convince me, but it didn't hurt her case either.

I pulled my fingers from her pussy, and she let go of my cock. Though the backseat of her car didn't exactly allow for a lot of room to move around, Lauren managed to swing one of her long, shapely legs over mine and climb on top of me. She bunched up her skirt around her waist with an eagerness that bordered on frantic, pulling her panties to the side. I was granted a view of her pussy lips, so pink and wet, framed by her nearly untamed bush of a fiery red that matched her hair. The scent of her arousal filled the car, intoxicating and enough to drive me wild.

I'd more or less been in this exact position before, but that didn't make it any less exciting to be in this position.

"You're so fucking hot..." I groaned as she leaned into me, gliding her pussy lips up and down my shaft.

"I know..." she replied, pulling my shirt off and tossing it aside with such force she almost took my glasses with her. Running her fingers down my recently defined chest and abs, she replied, "And you've grown into an exceptional young man."

I leaned in, kissing her. "I like to think I'm still an exceptional work in progress."

"Whatever you have to tell yourself," Lauren replied with a chuckle, reaching between her legs to grab my cock, guiding it toward her pussy. "I know what I know..."

I groaned as she rubbed my cockhead against her lips. She was so wet... so fucking hot... I needed her in this moment like I needed air to breathe, and I was well past the point where only a tease would suffice.

I hissed sharply as the head popped inside of her tight cunt, a sound that was soon drowned out by her loud moan. Lauren looked down at me with such want, such hunger, and began to lower herself slowly onto my cock.

Nothing could have held me back from feasting at this point. I leaned in, suckling at her nipples with my hands planted firmly on her ass, squeezing and massaging her as she continued her agonizingly sweet descent down my cock, pleasure flowing through my body as I filled her impressively tight pussy a little at a time. Her moans, her high whines and sharp intakes of air became a symphony to my ears as I continued to ravenously devour her tits.

Finally, she was seated on my lap completely, every inch of my cock buried deeply within me. Briefly there was silence, the only sounds filling the car her ragged breathing, and the sound of my mouth on her tits. Even this was stopped by Lauren when she pushed my head away from her chest, looking me in the eye as we took in this moment.

Ever since the two of us had started fucking around with each other, there had been a distinct intimacy between Lauren and me, and I could feel it now. Here we were, completely and utterly joined, and we couldn't stop looking each other in the eyes and sharing these slight smiles. Right here, like this, she suddenly looked younger, more alive than she often did back home, and in a moment that might also have been giddy, she leaned in and kissed me, throwing her arms around me to hold me close to her. It was a long, lingering kiss that brought out a warmth deep inside of me, one that only got hotter as her pussy muscles began to squeeze and massage my cock.

She held me there like this for quite a while, savoring this special heated intimacy the two of us shared, enjoying the feel of me being buried deep inside of her... but soon, she began to writhe in my lap. With the most impressively practiced skill, she rocked her hips, slowly bouncing up and down on my cock while building to a pace that I knew would get hot sooner rather than later, because while the two of us did share a certain intimacy, whenever we got hot and heavy with one another, we tended to fuck like maniacs.

Though she couldn't get very acrobatic considering the limited space we were in, Lauren more than made up for it with enthusiasm as she roughly rode me.

And as she indulged in her rarely used dirty talk.

"Oh fuck, oh fuck, I've missed this cock... I've missed this big fucking cock... god, I can't get this at home, I can't get fucked like this, not like I want, not like I deserve, god, this is amazing... you're amazing, Ryan, you fill me up, so deep, so fucking hard..." Lauren said, leaning into my face and making sure I had a mouth filled with tit.